Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P.B. No. 1603, Cochin 682018, Kerala, India.
Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P.B. No. 1603, Cochin 682018, Kerala, India.
Food Chem. 2018 Jun 15;251:125-134. doi: 10.1016/j.foodchem.2018.01.059. Epub 2018 Jan 10.
Bivalve black clam, Villorita cyprinoides is traditional seafood in Southwestern coast of Arabian Sea. In this study, bioactivity-guided purification of ethyl acetate:methanol extract of black clam was carried out. Two irregular meroterpenoids {tetrahydro-3-methoxy-5-((E)-8,12-dimethyloct-8-enyl)-pyran-2-one (1) and dihydro-5-(8-(9,12-dihydro-8-methyl-11-propyl-2H-pyran-8-yl)-ethyl)-furan-2(3H)-one (2)} and two hexahydro-isochromenyl-meroterpenoids (3-4) were identified. The structures were characterized by detailed spectroscopy and their antioxidant/anti-inflammatory potentials were evaluated. Compound 2 registered significantly greater 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging ability (IC <0.65 mg/mL) than other analogues (IC ≥0.70 mg/mL). Ferrous ion (Fe) chelating ability was higher for 1-2 (IC ∼0.84 mg/mL) than α-tocopherol (IC 0.89 mg/mL). The 5-lipoxygenase inhibitory potential of furano-meroterpenoid analogue, 2 (IC 0.76 mg/mL) was greater than other compounds (IC >0.90 mg/mL). An optimum hydrophobic-hydrophilic balance of furano-meroterpenoid and lesser steric bulk manifested towards its greater bioactivities compared to other compounds. These anti-inflammatory and antioxidant leads could be used as potential functional food components.
双壳黑蛤，Villorita cyprinoides 是阿拉伯海西南海岸的传统海鲜。在这项研究中，对黑蛤的乙酸乙酯：甲醇提取物进行了基于生物活性的纯化。分离得到两种不规则的倍半萜类化合物{四氢-3-甲氧基-5-((E)-8,12-二甲基辛-8-烯基）-吡喃-2-酮（1）和二氢-5-（8-（9,12-二氢-8-甲基-11-丙基-2H-吡喃-8-基）-乙基）-呋喃-2(3H)-one（2）}和两种六氢异苯并呋喃基倍半萜类化合物（3-4）。通过详细的光谱学特征对结构进行了表征，并评估了它们的抗氧化/抗炎潜力。化合物 2 在 2,2-二苯基-1-吡咯基肼（DPPH）自由基清除能力（IC <0.65mg/mL）方面优于其他类似物（IC ≥0.70mg/mL）。1-2（IC ∼0.84mg/mL）对亚铁离子（Fe）的螯合能力高于α-生育酚（IC 0.89mg/mL）。呋喃型倍半萜类似物 2 的 5-脂氧合酶抑制作用（IC 0.76mg/mL）大于其他化合物（IC >0.90mg/mL）。与其他化合物相比，呋喃型倍半萜的最佳疏水性-亲水性平衡和较小的空间位阻导致其具有更大的生物活性。这些抗炎和抗氧化的先导化合物可以作为潜在的功能性食品成分。
